Stereoselective synthesis of alcohols, XXII. E/Z??selectivity on addition of α??substituted allylboronates to aldehydes

RW Hoffmann, B Landmann

Index: Hoffmann, Reinhard W.; Landmann, Bernd Chemische Berichte, 1986 , vol. 119, # 3 p. 1039 - 1053

Full Text: HTML

Citation Number: 54

Abstract

Abstract α-Heterosubstituted allylboronates 7 are prepared. Addition of 7 to aldehydes results in E/Z-isomeric homoallyl alcohols 13 and 14. The reasons for the predominant formation of the Z-isomer 14 are discussed. The Z-bromo olefins 16 and 20 obtained in this way serve as starting point for chain extension or formation of δ-lactones 21.